This invention relates to sulfonylureas useful as herbicides and plant growth regulants. More particularly, it relates to o-thiocarbonylsulfonylureas having useful herbicidal and plant growth regulant activity.
U.S. Pat. No. 4,394,506 teaches herbicidal carboxylic ester sulfonylureas of the formula ##STR1## where, in part, Q is O, S or NR.sub.6 ;
R is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.2 -C.sub.6 alkyl substituted with 1-4 substituents selected from 0-3 atoms of F, Cl or Br, 0-2 methoxy groups and 0-1 cyano group; CH.sub.2 CI; CH(R.sub.7 ')CO.sub.2 CH.sub.3 or CH(R.sub.7 ')CO.sub.2 C.sub.2 H.sub.5 where R.sub.7 ' is H or CH.sub.3 ; C.sub.3 -C.sub.6 alkenyl substituted with 1-3 atoms of F, Cl or Br; etc. PA1 R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, NO.sub.2, etc. PA1 R.sub.3 is H, Cl, Br, F or CH.sub.3 ; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, allyl, CH.sub.2 CN or CH.sub.2 CH.sub.2 CN; and PA1 R and R.sub.6 can be taken together to form (CH.sub.2).sub.4, (CH.sub.2).sub.5, (CH.sub.2).sub.6, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 or CH.sub.2 CH.sub.2 N (CH.sub.3)CH.sub.2 CH.sub.2. PA1 R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; and PA1 W is O or S. PA1 R.sub.2 is H, Cl, Br, F, CF.sub.3 or OCH.sub.3 ; PA1 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl; PA1 W is O or S; PA1 R.sub.8 is H or CH.sub.3 ; etc. PA1 A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3 ; PA1 A is C(O)QR.sup.I or C(T)R.sup.II ; PA1 Q is O, S or NR.sub.6 ; PA1 R.sup.I is inter alia, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl; PA1 B is ##STR5## etc. PA1 R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, etc. PA1 R.sub.12 is H or CH.sub.3 ; PA1 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl, OR.sub.16, F, Cl, Br, etc.; PA1 E is a single bond or --CH.sub.2 --; PA1 Q is Q.sub.1, Q.sub.2 or Q.sub.3 ; PA1 Q.sub.1 is ##STR10## Q.sub.2 is ##STR11## Q.sub.3 is ##STR12## n is 0 or 1; W.sub.1 is O or S; R is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl, Cl, Br, F, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 CN, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.2 is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or phenyl; PA1 R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.a and R.sub.b may be taken together as (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5 or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 ; PA1 R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R.sub.4 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.2 -C.sub.6 alkyl substituted with 1-4 substitutents selected from PA1 CH.sub.2 CN, CH.sub.2 OR.sub.9, CH(R.sub.10)CO.sub.2 CH.sub.3, CH(R.sub.10)CO.sub.2 C.sub.2 H.sub.5, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, C.sub.4 -C.sub.10 cycloalkylalkyl, C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 CH.sub.3 groups, C.sub.5 -C.sub.6 cycloalkyl substituted with PA1 R.sub.8 is C.sub.1 -C.sub.2 alkyl; PA1 m is 0, 1 or 2; PA1 p is 0 or 1; PA1 w.sub.2 is O or S; PA1 R.sub.9 is C.sub.1 -C.sub.3 alkyl, chloroethyl, trichloroethyl, phenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 or ##STR15## R.sub.10 is H or CH.sub.3 ; R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.12 is H, F, Cl, Br, CH.sub.3, OCH.sub.3, SCH.sub.3, SO.sub.2 CH.sub.3, NO.sub.2 or CF.sub.3 ; PA1 R.sub.13 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.14 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.15 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.3 alkyl substituted with C.sub.1 -C.sub.3 alkoxy or phenoxy, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.5 -C.sub.6 cycloalkyl substituted with CH.sub.3 or OCH.sub.3, CH.sub.2 CN, CH.sub.2 CH.sub.2 CN, OCH.sub.3, OC.sub.2 H.sub.5 N(CH.sub.3).sub.2 ##STR16## R.sub.16 is H C.sub.1 -C.sub.6 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CN or CH.sub.2 CH.sub.2 CN; or PA1 R.sub.15 and R.sub.16 may be taken together to form (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5, (CH.sub.2).sub.6, CH.sub.2 CH.dbd.CHCH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 or CH.sub.2 CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 ; PA1 R.sub.17 is H or CH.sub.3 ; PA1 R.sub.18 is H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.19 is H, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, F, Br, Cl, CF.sub.3, CN, NO.sub.2, SO.sub.2 CH.sub.3, SCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 A is ##STR17## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di (C.sub.1 -C.sub.3)alkylamino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, ##STR18## W.sub.3 and W.sub.4 are independently O or S; q is 2 or 3; PA1 R.sub.d is H or CH.sub.3 ; PA1 R.sub.e is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.f is C.sub.1 -C.sub.2 alkyl; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 Z.sub.1 is CH or N; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 and their agriculturally suitable salts; PA1 Q is Q.sub.1. PA1 Q is Q.sub.2 or Q.sub.3. PA1 W is O; PA1 R is H; and PA1 the carbon of R.sub.4 bonded to W.sub.1 is also bonded to at least one hydrogen. PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, Br, F, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5, cyclopropyl, ##STR20## OCF.sub.2 H, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3. PA1 R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 substituents selected from 0-3 atoms of F or Cl, 0-2 OCH.sub.3 or 0-1 CN, or C.sub.3 -C.sub.4 alkenyl substituted with 1-3 Cl. PA1 R.sub.2 is H; and PA1 R.sub.1 is in the 5-position and selected from H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA1 R.sub.1 is H, Cl, CH.sub.3 or OCH.sub.3 ; PA1 n is O; and PA1 E is a single bond. PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 C.tbd.CH, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3. PA1 Q is --C(S)W.sub.1 R.sub.4 ; and PA1 W.sub.1 is S. PA1 Q is --C(S)W.sub.1 R.sub.4 ; and PA1 W.sub.1 is O. PA1 W is O; PA1 R is H; and PA1 is other than C(CH.sub.3).sub.3. PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, Br, F, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5, cyclopropyl, ##STR21## OCF.sub.2 H, SCF.sub.2 H, C.tbd.CH or C.tbd.CCH.sub.3. PA1 R.sub.15 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA1 R.sub.16 is H, C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2, or PA1 R.sub.15 and R.sub.16 are taken together to form (CH.sub.2).sub.4, (CH.sub.2).sub.5 or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2. PA1 R.sub.2 is H; and PA1 R.sub.1 is in the 5-position and selected from H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub. -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3 OC.sub.2 H.sub.5, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2 PA1 R.sub.1 is H, Cl, CH.sub.3 or OCH.sub.3 ; PA1 n is O; and PA1 E is a single bond. PA1 R.sub.13 is C.sub.1 -C.sub.2 alkyl: PA1 R.sub.14 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.15 is H or C.sub.1 -C.sub.3 alkyl; and PA1 R.sub.16 is H or C.sub.1 -C.sub.3 alkyl. PA1 Q is --C(S)NR.sub.15 R.sub.16. PA1 Q is --C(.dbd.NR.sub.13)W.sub.1 R.sub.14.
U.S. Pat. No. 4,348,219 discloses herbicidal phenylacetic ester sulfonylureas of the formula ##STR2## wherein L is CO.sub.2 R.sub.10 CONR.sub.3 R.sub.4 or CN;
U.S. Pat. No. 4,420,325 covers herbicidal benzylsulfonylureas of the formula ##STR3## wherein R.sub.1 is inter alia, F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl;
U.S Pat. No. 4,481,029 teaches herbicidal sulfonylureas of Formulae I, II and III: ##STR4## wherein W' is O or S;
European Patent Application No. 95,925 (published Dec. 7, 1983) discloses, in part, herbicidal sulfonylureas of the formula ##STR6## wherein Q is, inter alia, ##STR7## R is H or CH.sub.3 ; R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, etc.;
R.sub.15 is H or CH.sub.3 ; etc.
U.S. Pat. Nos. 4,544,401 and 4,435,206 disclose herbicidal pyridinesulfonylureas.
The presence of undesired vegetation causes substantial damage to useful crops. especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials, useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing signficant damage to useful crops.